Gallocyanin dye and process of making.



UNITED STATES PATENT OFFICE.

WILHELM LOMMEL, OF ELBERFELD, GERMANY, ASSIGNOR TO FARBENFABRIKEN VORM.FRIEDR. BAYER & (30., OF ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

GALLOCYANIN DYE AND PROCESS OF MAKING.

Specification of Letters latent.

No Drawing. Original application filed December 8, 1908, Serial No.466,489.

- filed June 16, 1909.

Patented Oct. 5, 1909.

Divided and this application Serial No. 502,522.

To all whom it may concern:

Be it known that I, WVILHELM LOMMEL, doctor of philosophy, chemist,citizen of the German Empire, residing at Elberfeld, Germany, haveinvented new and useful Improvements in Gallocyanin Dye, of which thefollowing is a specification.

My invention relates to the production of sulfonic acids from oxidizedcondensation products of gallocyanins and amins.

The present application, which is a divisional application from myapplication Serial No. 466,489, filed December 8th, 1908, coversspecifically the new dyestuffs produced from gallocyanin obtained fromnitrosodiethyl-anilin and gallic acid.

The diethylgallocyanin color is first condensed with an aromatic amin atordinary temperature and the compound thus produced is oxidized by acurrent of atmospheric air or oxygen. A carrier of oxygen 6. g. amanganese, iron or vanadium compound may be added to the mass tofacilitate the reaction, and the oxidation can also be carried onsimultaneously with the reaction of condensation. The substances thusobtained have probably the following general formula, in which It meansan aromatic radical.

By heating these products, the carboxyl group is split off. Afterheating the substances are finally sulfonated, the sulfo group enteringinto the molecule of the aromatic amin and thus giving coloring matterspossessmg can/Mar The new dyestuffs possess exceedingly bright and clearblue shades and are of special value for printing, being. very fast tothe action of chlorin. They are in the shape of their alkaline saltsdark powders soluble in water with a blue color and in concentratedsulfuric acid with a reddish color and giving in printing on chromemordants generally blue shades.

In order to illustrate the new process more fully, I give the followingexample, the parts being by weight: parts of gallocyanin (obtained fromnitrosodiethylanilin and gallic acid) are introduced into 300 parts ofanilin and a current of air is conducted through the cold mixture whilestirring well, so that contact with the air is facilitated. Thecondensation product is then isolated in a pure state and with anexcellent yield. It is soluble in concentrated sufuric acid with aviolet color and does not melt on heating it to 200 C. In order to splitoff the carboxylic group the isolated condensation product or the massof the reaction is slowly heated to about 100 C. 50 parts of the thusproduced gallocyanin anilid are then stirred into 200 parts of fumingsulfuric acid (25 per cent. S0,) at a temperature of l0-l5 C. The massof the reaction is then slowly heated to from 3040 C. while stirringuntil a test portion is soluble in a dilute sodium carbonate solution.

The mass of the reaction is poured into water, the sulfonic acid isfiltered olf and transformed into its ammonium salt which is a brownpowder soluble in water with a pure blue and in concentrated sulfuricacid with a magenta-red color.

The new dyestulf dyes chromed wool beautiful fast green-blue shades andproduces when printed with chromium compounds on cotton fast green-blueshades.

Instead of anilin, other amins e. g. toluidins, chloroanilins etc. canbe used.

I claim:

1. The herein described process for the manufacture of new dyestuffs,which process consists in condensing and oxidizing gallocyanin made bymeans of gallic acid and nitrosodiethylanilin at ordinary temperaturewith aromatic amins, heating them to split off the carboxylic group, andfinally sulfonating them, substantially as described.

2. The herein described process for the manufacture of a dyestuff, whichprocess consists in condensing and oxidizing gallocyanin made by meansof gallic acid and nitrosodiethylanilin with anilin at ordinarytemperature, heating it to split off the carboxylic group, and finallysulfonating it, substantially as described.

3. The herein described new dyestuff sulfonic acids obtainable fromgallocyanin made by means of gallic acid and nitrosodiethylanilin, whichdyestuffs are in the shape of their alkaline salts dark powders solublein water with a blue color, and in concentrated sulfuric acid with areddish color, characterized by great clearness of their shades andremarkable fastness to the action of chlorin; and giving in printingwith chrome-mordants on cotton fast blue shades, substantially asdescribed.

4. The herein described new dyestuff sulfonic acid obtainable fromanilin and the gallocyanin made by means of gallic acid andnitrosodiethylanilin, which dyestuff is in the shape of its ammoniumsalt a brown powder soluble in water with a pure blue, and inconcentrated sulfuric acid with a magenta-red color; dyeing chromed woola clear fast green-blue shade, remarkably fast to the action of chlorin,and giving in printing with chromemordants on cotton fast green-blueshades, substantially as described.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing witnesses.

lVILI-IELM LOMMEL. [L. s] Witnesses OTTO KONIG, C. J. lVRIcH'r.

